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化学进展 2013, Vol. 25 Issue (05): 707-716 DOI: 10.7536/PC120935 前一篇   后一篇

• 综述与评论 •

聚苯乙烯固载过渡金属催化剂在硅氢加成和加氢反应中的应用

张淑芳, 白赢, 彭家建, 胡应乾*, 来国桥*   

  1. 杭州师范大学有机硅化学及材料技术教育部重点实验室 杭州 310012
  • 收稿日期:2012-09-01 修回日期:2012-11-01 出版日期:2013-05-24 发布日期:2013-04-15
  • 通讯作者: 胡应乾, 来国桥 E-mail:yingqianhu@hznu.edu.cn;gqlai@hznu.edu.cn
  • 基金资助:

    浙江省钱江人才计划项目(No. 2009R10021)和杭州市科技计划项目(No. 20090231T01)资助

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Application of Polystyrene Immobilized Transition Metals as Catalysts for Hydrosilylation and Hydrogenation

Zhang Shufang, Bai Ying, Peng Jiajian, Hu Yingqian*, Lai Guoqiao*   

  1. Key Laboratory of Organosilicon Chemistry and Materials Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China
  • Received:2012-09-01 Revised:2012-11-01 Online:2013-05-24 Published:2013-04-15

聚苯乙烯树脂具有优良的物理化学性能,其与过渡金属的络合物在硅氢加成和催化加氢反应中得到了广泛应用,表现出良好的催化活性、反应选择性和重复使用性能,具有均相催化剂和其他固载型催化剂不具备的优势。利用含配位基团的化合物对聚苯乙烯改性后,可显著提高对金属的配位能力以及催化剂的稳定性,也往往表现出更好的催化性能。鉴于近年来聚苯乙烯固载的过渡金属催化剂在硅氢加成和催化加氢反应中的研究较为引人注目,本文对该类催化剂的制备方法、催化性能及相关机理进行了总结和分析。首先介绍了经胺、膦、巯基、不饱和烃等改性的聚苯乙烯固载的过渡金属催化剂在硅氢加成反应中的应用,其次介绍了聚苯乙烯固载的铂、钯、铑、钌、纳米金、铬、双金属胶体等在催化加氢反应中的应用,重点介绍了聚苯乙烯树脂与金属钯、铑的固载型催化剂,最后对该类催化剂的发展方向进行了分析和展望。

关键词： 聚苯乙烯, 催化剂, 硅氢加成, 催化加氢

Polystyrene resin has been widely employed as carriers of transition metals due to its excellent physical and chemical properties. The obtained polystyrene-immobilized transition metal complexes generally exhibit high catalytic activity, enhanced reaction selectivity and good reusability, and thus have been attracting great attention for improving the efficiency of hydrosilylation and hydrogenation reactions in recent years. In addition, modifying polystyrene by coordinating-group-containing compounds could significantly enhance the coordination ability to metal ions. Consequently, the resultant catalysts usually provide better catalytic performance. In view of this, the current review summarizes the novel progress for the synthesis and application of polystyrene-immobilized transition metal complexes as catalysts in hydrosilylation and hydrogenation. The preparation method, catalytic performance and the related mechanism are introduced. Firstly, the amine-, phosphine-, mercapto groups-, and unsaturated hydrocarbon-modified polystyrene immobilized transition metals for catalytic hydrosilylation are described. Secondly, polystyrene immobilized transition metals (including Pt, Pd, Rh, Ru, Au nanoparticles, Cr, etc.) for catalytic hydrogenation are described, with the emphasis on the complexes of Pd and Rh. At last, the development trend of this kind of catalysts is suggested. Contents
1 Introduction
2 Application of polystyrene immobilized transition metals as catalysts for hydrosilylation
2.1 Polystyrene immobilized transition metal catalysts modified by amine
2.2 Polystyrene immobilized transition metal catalysts modified by phosphine
2.3 Polystyrene immobilized transition metal catalysts modified by mercapto groups
2.4 Polystyrene immobilized transition metal catalysts modified by unsaturated hydrocarbon
2.5 Others
3 Application of polystyrene immobilized transition metals as catalysts for hydrogenation
3.1 Polystyrene-Pt catalysts
3.2 Polystyrene-Pd catalysts
3.3 Polystyrene-Rh catalysts
3.4 Polystyrene-Ru catalysts
3.5 Polystyrene-Au catalysts
3.6 Polystyrene-Cr catalysts
3.7 Polystyrene-Au/Pd catalysts
4 Conclusion and outlook

Key words: polystyrene, catalysts, hydrosilylation, hydrogenation

中图分类号: 

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[1] Capka M, Svoboda P, Cerny M. Tetrahed. Lett., 1971, 12(50): 4787-4790
[2] Capka M, Svoboda P, Kraus M. Chem. Ind., 1972, (16): 650
[3] Drake R, Dunn R, Sherrington D C, Thomson S J. Chem. Commun., 2000, (19): 1931-1932
[4] Drake R, Dunn R, Sherrington D C, Thomson S J. J. Mol. Catal. A: Chem., 2001, 177(1): 49-69
[5] Drake R, Sherrington D C, Thomson S J. J. Chem. Soc. Perkin Trans., 2002, (13): 1523-1534
[6] Drake R, Sherrington D C, Thomson S J. React. Funct. Polym., 2004, 60: 65-75
[7] 戴延凤(Dai Y F), 李磊(Li L), 李凤仪(Li F Y). 化工进展(Chemical Industry and Engineering Progress), 2006, 25(1): 74-77
[8] Cullen W R, Han N F. J. Organometal. Chem., 1987, 333(2): 269-280
[9] Dumont W, Paulin J C, Dang T P. J. Am. Chem. Soc., 1973, 95(25): 8295-8299
[10] 阚成友(Kan C Y), 袁青(Yuan Q), 杨勇(Yang Y), 孔祥正(Kong X Z). 高等学校化学学报(Chemical Journal of Chinese Universities), 1995, 16(11): 1806-1809
[11] Kan C Y, Yuan Q, Luo A G, Kong X Z. Polym. Adv. Techn., 1996, 7(2): 76-78
[12] Kan C Y, Du C M, Kong X Z. Polym. J., 2002, 34(3): 97-102
[13] 洪曼青(Hong M Q), 杜池敏(Du C M), 赵培真(Zhao P Z), 孔祥正(Kong X Z), 阚成友(Kan C Y). 有机硅材料(Silicone Material), 2000, 14(2): 10-13
[14] 阚成友(Kan C Y), 袁青(Yuan Q), 王颖(Wang Y), 贝小来(Bei X L). 有机硅材料及应用(Silicone Material & Applications), 1995, (2): 16-17
[15] 阚成友(Kan C Y), 杜池敏(Du C M), 刘德山(Liu D S). 有机硅材料(Silicone Material), 2002, 16(1): 1-4
[16] Kishi K, Ishimaru T, Ozono M, Tomita I, EdnoT. J. Polym. Sci. Part A: Polym. Chem., 2000, 38(1): 35-42
[17] Kowalewska A. J. Organometal. Chem., 2008, 693(12): 2193-2199
[18] Wawrzyńczak A, Dutkiewicz M, Guliński J, Maciejewski H, Marciniec B, Fiedorow R. Catalysis Today, 2011, 169(1): 69-74
[19] 陈远荫(Chen Y Y), 张宝莲(Zhang B L), 唐星华(Tang X H), 卢雪然(Lu X R). 离子交换与吸附(Ion Exchange and Adsorption), 1998, 14(3): 246-249
[20] 陈远荫(Chen Y Y), 孟令芝(Meng L Z), 柯爱青(Ke A Q). 催化学报(Chinese Journal of Catalysis), 1997, 18(2): 144-146
[21] 孟令芝(Meng L Z), 柯爱青(Ke A Q), 陈远荫(Chen Y Y). 应用化学(Chinese Journal of Applied Chemistry), 1997, 14(1): 107-109
[22] Török B, Kulkarni A, Sousa R D, Satuluri K, Török M, Prakash G K S. Catal. Lett., 2011, 141(10): 1435-1441
[23] Chen C W, Serizawa T, Akashi M. Chem. Mater., 1999, 11(5): 1381-1389
[24] Bhaduri S, Darshane V S, Sharmab K, Mukesh D. Chem. Commun., 1992, (23): 1738-1740
[25] Bykov A, Matveeva V, Sulman M, Valetskiy P, Tkachenko O, Kustov L, Bronstein L, Sulman E. Catalysis Today, 2009, 140(1/2): 64-69
[26] Andersson C, Larsson R. J. Am. Oil Chem. Soc., 1981, 58(6): 675-680
[27] Jo Y D, Ahn J H, Ihm S K. Korean J. Chem. Eng., 1997, 14(2): 125-128
[28] Alexander S, Udayakumar V, Gayathri V. Transition Met. Chem., 2012, 37(4): 367-372
[29] Nakao R, Rhee H, Uozumi Y. Org. lett., 2005, 7(1): 163-165
[30] 杨士勇(Yang S Y), 孙君坦(Sun J T), 李弘(Li H), 何炳林(He B L). 高分子学报(Acta Polymerica Sinica), 1989, (5): 572-578
[31] 胡卫兵(Hu W B), 周忠信(Zhou Z X), 李翔(Li X), 张曼征(Zhang M Z). 离子交换与吸附(Ion Exchange and Adsorption), 1995, 11(2): 117-121
[32] 何炳林(He B L), 王俐(Wang L). 高分子学报(Acta Polymerica Sinica), 1990, (1): 30-35
[33] 何炳林(He B L), 王俐(Wang L). 高分子学报(Acta Polymerica Sinica), 1987, (5): 404-408
[34] 潘才元(Pan C Y), 冯品珍(Feng P Z), 梁冰玉(Liang B Y). 催化学报(Chinese Journal of Catalysis), 1981, 2(2): 152-155
[35] 茅素芬(Mao S F), 陈宗翰(Chen Z H), 江英彦(Jiang Y Y). 西安交通大学学报(Journal of Xi’an Jiaotong University), 1989, 23(2): 113-120
[36] 张一平(Zhang Y P), 徐筠(Xu J), 廖世健(Liao S J), 袁华先(Yuan H X), 李悟崇(Li W C). 分子催化(Journal of Molecular Catalysis), 1991, 5(4): 362-366
[37] Sulman E, Bodrova Y, Matveeva V, Semagina N, Cerveny L, Kurtc V, Bronstein L, Platonova O, Valetsky P. Appl. Catal. A: General, 1999, 176(1): 75-81
[38] Bombi G, Lora S, Zancato M, D’Archivio A A, Jerabek K, Corain B. J. Mol. Catal. A: Chem., 2003, 194(1/2): 273-281
[39] Semikolenov V A, Likholobov V A, Valentini G, Braca G, Ciardelli F. React. Kinet. Catal. Lett., 1980, 15(3): 383-388
[40] Heldal J A, Moulton K J, Frankel E N. J. Am. Oil Chem. Soc., 1989, 66(7): 979-982
[41] Kaneda K, Terasawa M, Imanaka T, Teranishi S. Chem. Lett., 1976, 5(9): 995-998
[42] Kaneda K, Mizugaki T. Organometallics, 1996, 15(15): 3247-3249
[43] Krause H W. React. Kinet. Catal. Lett., 1979, 10(3): 243-246
[44] Parameswaran V R, Vancheesan S. React. Kinet. Catal. Lett., 1991, 44(1): 185-190
[45] Parameswaran V R, Vancheesan S. React. Kinet. Catal. Lett., 1991, 45(1): 55-60
[46] Parameswaran V R, Vancheesan S. Proc. Indian Acad. Sci. (Chem. Sci. ), 1991, 103(2): 99-106
[47] Bhaduri S, Lahiri G K, Munshi P. J. Organometal. Chem., 2000, 606(2): 151-155
[48] Nunes R M D, Fernandes T F, Carvalho G A, Santos E N, Moreno M J S M, Piedade A P, Pereira M M. J. Mol. Catal. A: Chem., 2009, 307(1/2): 115-120
[49] Norma A C, Gerardo A, Miguel P H, Ratnasamy S. Tetrahed. Lett., 2009, 50(19): 2228-2231
[50] Fish R H, Thormondsen A D, Heinemann H. J. Mol. Catal., 1985, 31(2): 191-198
[51] Itsuno S, Tsuji A, Takahashi M. Tetrahed. Lett., 2003, 44(19): 3825-3828
[52] Islam S M, Tuhina K, Mubarak M, Mondal P. J. Mol. Catal. A: Chem., 2009, 297(1): 18-25
[53] Arakawa Y, Haraguchi N, Itsuno S. Tetrahed. Lett., 2006, 47(19): 3239-3243
[54] Takahashi Y, Yukita W, Chatterjee M, Suzuki T M. React. Funct. Polym., 2008, 68(10): 1476-1482
[55] Panigrahi S, Basu S, Praharaj S, Pande S, Jana S, Pal A, Ghosh S K, Pal T. J. Phys. Chem. C, 2007, 111(12): 4596-4605
[56] Pittman C U J, Kim B T, Douglas W M. J. Org. Chem., 1975, 40(5): 590-593
[57] Seregina M V, Bronstein L M, Platonova O A, Chernyshov D M, Valetsky P M. Chem. Mater., 1997. 9(4): 923-931
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